HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 1-[4-(2,4-Dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | (2,4-Dimethoxypyrimidin-5-yl)boronic acid | HCID 2736209 | — |
| Reactant | 1-(4-Bromo-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester | HCID 58906471 | — |
| Reactant | 1-[4-(2,4-Dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester | HCID 59744269 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | 1-[4-(2,4-Dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester | HCID 59744269 | — |
| Product | 1-[4-(2,4-Dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride salt | HCID 69063525 | — |
Reaction Steps
1-[4-(2,4-Dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 25 was synthesized by the Suzuki coupling of 1-(4-bromobenzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 1 with 2,4-dimethoxypyrimidine-5-boronic acid 24 using Palladium(II) acetate, triphenylphosphine, and Na2CO3. Reaction of compound 25 with 2 M HCl solution in diethylether yielded 1-[4-(2,4-dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride salt 26 (Scheme-7).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08507523B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-a7c6a07309c54480bbaf9880bdda6277 |
| Source note | uspto-grants-2013_08 |